raffish

Someone raffish is a bit of a scoundrel, carelessly making mischief. Your raffish classmate might constantly play mean practical jokes, always denying responsibility with a charming smile.

If you're raffish, you're a "rake" or a "cad." Though you're pretty much bad news, you pull off your dastardly deeds in an attractive manner. Someone with a raffish look is intriguing as well as disreputable. Raffish comes from riff-raff, "generally undesirable people," from the Medieval French rifle et rafle, "stealing from the bodies of the dead on the battlefield."

Primary Meanings of raffish

1.
adj
marked by a carefree unconventionality or disreputableness
2.
adj
marked by up-to-dateness in dress and manners
Full Definitions of raffish
1

adj marked by a carefree unconventionality or disreputableness

“"a cocktail party given by some... raffish bachelors"- Crary Moore”
Synonyms:
devil-may-care, rakish
unconventional
not conventional or conformist
2

adj marked by up-to-dateness in dress and manners

Synonyms:
dapper, dashing, jaunty, natty, rakish, snappy, spiffy, spruce
fashionable, stylish
being or in accordance with current social fashions

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